diff --git a/config/software/ruby-windows-devkit.rb b/config/software/ruby-windows-devkit.rb
index b6d0fbfb5..713fcc0e0 100644
--- a/config/software/ruby-windows-devkit.rb
+++ b/config/software/ruby-windows-devkit.rb
@@ -62,8 +62,12 @@
     "liblzma-1.dll" => "liblzma-1.dll",
     "libbz2-2.dll" => "libbz2-2.dll",
     "libz-1.dll" => "libz-1.dll",
+    "libssp-0.dll" => "libssp-0.dll",
   }.each do |target, to|
     copy "#{install_dir}/embedded/mingw/bin/#{to}", "#{install_dir}/bin/#{target}"
+
+    copy "#{install_dir}/embedded/bin/x64-msvcrt-ruby300.dll", "#{install_dir}/bin/x64-msvcrt-ruby300.dll"
+    copy "#{install_dir}/embedded/mingw/include/ansidecl.h", "#{install_dir}/embedded/mingw/x86_64-w64-mingw32/include/ansidecl.h"
   end
 
   # IIS 8.5 Server STIG finding V-76717 warns on this file because it ends with